title: The triflic acid-mediated cyclization reactions of N-cinnamoyl-1-naphthylamines.
abstract: N-cinnamoyl-1-naphthylamines undergo a cyclization reaction with triflic acid to form 4-phenyl-3,4-dihydro-1H-naphth[1,8-bc]azepin-2-ones and 4-phenyl-3,4-dihydro-1H-benzo[h]quinolin-2-ones. However, the N-benzyl analogues also undergo a unique cascade reaction to form novel heptacyclic structures via a 1,2-addition followed by a 4-addition to the naphthalene. With an electron-rich N-benzyl substituent, the heptacycle is the sole product.
authors.affiliation: Department of Chemistry, University College London , 20 Gordon Street, London WC1H 0AJ, U.K.
authors.forename: Frank D
authors.initials: FD
authors.lastname: King
authors.forename: Abil E
authors.initials: AE
authors.lastname: Aliev
authors.forename: Stephen
authors.initials: S
authors.lastname: Caddick
authors.forename: Derek A
authors.initials: DA
authors.lastname: Tocher
mesh_terms: D000588:Amines / Q000737:chemistry*; D002934:Cinnamates / Q000737:chemistry*; D003500:Cyclization; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*
chemical_list: D000588:Amines; D002934:Cinnamates; D008698:Mesylates; D009281:Naphthalenes; C031721:naphthalene; C012077:trifluoromethanesulfonic acid